1: NaH; 15-crown-6 / tetrahydrofuran / -30 °C 2: LiAlH4 View Scheme

1: LiAlH4 / diethyl ether 2: 42 percent / PBr3, pyridine / diethyl ether 3: 60 percent / dimethylsulfoxide 4: 67 percent / KOH / ethane-1,2-diol; H2O; ethanol / 18 h / Heating 5: 86 percent / oxalyl chloride, pyridine / benzene / 2 h / Ambient temperature 6: 76 percent / triethyl amine / diethyl ether / 1 h / Ambient temperature 7: 82 percent / diethyl ether / Ambient temperature 8: 17 percent / acetonitrile / Irradiation View Scheme

1: 85 percent / NaH / tetrahydrofuran / 0 deg C, then Rt 1 h 2: 1.) Dibal; 2.) silica gel / 1.) petroleum ether, hexane, -60 deg C, then 10 deg C over 1.5 h; 2.) petroleum ether, hexane, water, -30 deg C, then 0 deg C, 1 h 3: NaOH / 2.5 h / Ambient temperature 4: 75 percent / conc. H2SO4 / nitromethane / 0.25 h / 0 °C View Scheme

1: 6-methyl-hept-5-en-2-one; Methyltriphenylphosphonium bromide With n-butyllithium in tetrahydrofuran T=-78°C; 0.75 h; 2: With sec.-butyllithium in tetrahydrofuran T=-78°C; 1 h; 3: formaldehyd in tetrahydrofuran T=0 - 20°C;

1: NaH; 15-crown-6 / tetrahydrofuran / -30 °C 2: LiAlH4 View Scheme

1.1: NaH / tetrahydrofuran / 0 - 20 °C 1.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C 2.1: 86 percent / conc. H2SO4 / nitromethane / 0.5 h / 0 °C 3.1: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C 4.1: 96.5 percent / LDA / tetrahydrofuran / -40 - 20 °C 5.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C 6.1: p-toluenesulfonic acid; trimethyl orthoformate 6.2: 89 percent / HCl / acetone 7.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C 8.1: nBuLi / tetrahydrofuran / -20 °C 8.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C 10.1: 97 percent / HCl / acetone; H2O 11.1: LDA / tetrahydrofuran / 0.17 h / -20 °C 11.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C 12.1: HBr / CH2Cl2 / 0 °C 13.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C 14.1: 55 percent / various solvent(s) / 20 h / 63 °C View Scheme

barium dihydroxide; ethanol Umsetzung mit CH3MgI, Behandlung mit Phthalsaeureanhydrid bei 150grad und anschliessende Verseifung;

1: benzene; piperidine / unter Entfernen des entstehenden Wassers und anschliessenden Erhitzen in Gegenwart von Kupfer 2: lithium alanate; diethyl ether View Scheme

in isopropyl alcohol T=50°C; 24 h; ADH T. brockii (growing), NADP, PAN 800;

phosphate buffer; D-glucose; Pichia miso IAM 4682 (cells) in various solvent(s) T=30°C; 8 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;